(1SR,3RS,3aSR,6aRS)-Methyl 5-methyl-4,6-dioxo-3-[2-(trifluoro­meth­yl)phen­yl]octa­hydro­pyrrolo­[3,4-c]pyrrole-1-carboxyl­ate

Kudryavtsev, K.V.; Ivantcova, P.M.; Churakov, A.V.

doi:10.1107/S1600536812051471

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages o161-o162

doi:10.1107/S1600536812051471

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(1SR,3RS,3aSR,6aRS)-Methyl 5-methyl-4,6-dioxo-3-[2-(trifluoromethyl)phenyl]octahydropyrrolo[3,4-c]pyrrole-1-carboxylate

Konstantin V. Kudryavtsev,^a,^b ^* Polina M. Ivantcova ^a and Andrei V. Churakov ^c

^aDepartment of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russian Federation, ^bInstitute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka 142432, Moscow Region, Russian Federation, and ^cInstitute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii prosp. 31, Moscow 119991, Russian Federation
^*Correspondence e-mail: kudr@org.chem.msu.ru

(Received 16 December 2012; accepted 20 December 2012; online 4 January 2013)

In the title compound, C₁₆H₁₅F₃N₂O₄, the relative stereochemistry of the four stereogenic C atoms has been determined. The carboxymethyl and 2-(trifluoromethyl)phenyl substituents of the pyrrolidine cycle have a cis mutual arrangement. The five-membered saturated azacycle adopts an envelope conformation with the N atom occupying the flap position. In the crystal, adjacent molecules are combined in centrosymmetric dimers by two weak N—H⋯O hydrogen bonds.

Related literature

For general background to the chemistry affording bicyclic pyrrolo[3,4-c]pyrrole-based scaffolds and structural determination, see: Kudryavtsev & Irkha (2005 ); Kudryavtsev (2008 ); Kudryavtsev & Zagulyaeva (2008 ); Kudryavtsev et al. (2011 ).

Experimental

Crystal data

C₁₆H₁₅F₃N₂O₄
M_r = 356.30
Orthorhombic, P b c a
a = 11.6168 (4) Å
b = 12.7385 (5) Å
c = 21.2429 (8) Å
V = 3143.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 150 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.955, T_max = 0.968
28987 measured reflections
4585 independent reflections
3698 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.115
S = 1.05
4585 reflections
286 parameters
All H-atom parameters refined
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.884 (15)	2.363 (15)	3.1738 (13)	152.5 (13)
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812051471/ff2094sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051471/ff2094Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812051471/ff2094Isup3.cml

checkCIF report

Comment top

The core of the title compound is formed by two fused pyrrolidine cycles. It was effectively synthesized by the three-component approach developed by the authors (Fig. 1). Combination of molecular sieves and triethyamine represents an efficient reagent for performing three-component interaction of benzaldehyde, glycine ester and dipolarophile. The product X-ray structure determination indicates that cycloaddition step proceeds as endo-process (Fig. 2). Tetrasubstituted pyrrolidine cycle adopts envelope conformation with N1 atom occupying flap position. Amine atom N1 has trigonal pyramidal environment with the sum of valent angles equal to 329.0 °. Hydrogen atom H1 lies in axial position (relative to the mean plane of five-membered ring). As expected, dioxopyrrolidine cycle is planar within 0.0354 (7) Å.

In the crystal, the adjacent molecules are combined in centrosymmetric dimers by two weak N—H···O hydrogen bonds (Fig. 3). The same dimers were previously observed in the structure of (1SR,3RS,3aSR,6aRS-methyl 5-methyl-4,6-dioxo-3-phenyloctahydropyrrolo [3,4-c]pyrrole-1-carboxylate (Kudryavtsev & Zagulyaeva, 2008).

Related literature top

For general background to the chemistry affording bicyclic pyrrolo[3,4-c]pyrrole-based scaffolds and structural determination, see: Kudryavtsev & Irkha (2005); Kudryavtsev (2008); Kudryavtsev & Zagulyaeva (2008); Kudryavtsev et al. (2011).

Experimental top

Triethylamine (0.340 ml, 2.41 mmol) was added to the stirred mixture of 2-(trifluoromethyl)benzaldehyde (200 mg, 1.15 mmol), N-methylmaleimide (130 mg, 1.15 mmol), glycine methyl ester hydrochloride (158 mg, 1.30 mmol) and 4 Å molecular sieves (200 mg) in toluene under argon atmosphere. Reaction mixture was stirred for 48 h. Volatiles were removed at reduced pressure. CH₂Cl₂ (50 ml) was added to the residue, resulted suspension was filtered through Celite, washed with saturated solution of NH₄Cl (2 x 10 ml). Organic phase was dried over Na₂SO₄, concentrated and purified by column chromatography on silica gel 60 (particle size 0.040–0.063 mm) using CH₂Cl₂—MeOH (100:1) as eluent. Yield 168 mg (41%), colorless crystals, mp 183–185°C. ¹H NMR (400 MHz, CDCl₃): δ 2.61 (s, 3H, NCH₃), 3.28 (t, 1H, H-3a, J 8.2), 3.40 (t, 1H, H-6a, J 7.3), 3.64 (s, 3H, OCH₃), 3.95 (d, 1H, H-1, J 6.7), 4.59 (d, 1H, H-3, J 8.6), 7.20 (t, 1H, Ar, J 7.6), 7.30 (t, 1H, Ar, J 7.6), 7.61 (d, 1H, Ar, J 7.6). ¹³C NMR (100 MHz, CDCl₃): δ 24.94, 47.31, 48.92, 52.26, 58.89, 61.04, 123.02, 125.89, 128.06, 128.23, 131.96, 135.74, 169.84, 174.30, 175.78. Found, %: C, 54.12; H, 4.27; N, 7.78. C₁₆H₁₅F₃N₂O₄. Calculated, %: C, 53.94; H, 4.24; N, 7.86. The crystals were obtained by slow evaporation of the CDCl₃ solution.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Synthetic scheme.
	Fig. 2. The molecular structure of the title compound, showing the numbering scheme adopted. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 3. Hydrogen-bonded dimers in the structure of the title compound. H-bonds are shown as dashed lines. [Symmetry code: (i) 1 - x, 2 - y, 1 - z.]

(1SR,3RS,3aSR,6aRS)-Methyl 5-methyl-4,6-dioxo-3-[2-(trifluoromethyl)phenyl]octahydropyrrolo[3,4- c]pyrrole-1-carboxylate top

Crystal data top

C₁₆H₁₅F₃N₂O₄	F(000) = 1472
M_r = 356.30	D_x = 1.506 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7037 reflections
a = 11.6168 (4) Å	θ = 2.6–30.2°
b = 12.7385 (5) Å	µ = 0.13 mm⁻¹
c = 21.2429 (8) Å	T = 150 K
V = 3143.5 (2) Å³	Block, colourless
Z = 8	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker SMART APEXII diffractometer	4585 independent reflections
Radiation source: fine-focus sealed tube	3698 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 30.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
T_min = 0.955, T_max = 0.968	k = −17→16
28987 measured reflections	l = −29→29

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: difference Fourier map
wR(F²) = 0.115	All H-atom parameters refined
S = 1.05	w = 1/[σ²(F_o²) + (0.0599P)² + 0.958P] where P = (F_o² + 2F_c²)/3
4585 reflections	(Δ/σ)_max = 0.001
286 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₆H₁₅F₃N₂O₄	V = 3143.5 (2) Å³
M_r = 356.30	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.6168 (4) Å	µ = 0.13 mm⁻¹
b = 12.7385 (5) Å	T = 150 K
c = 21.2429 (8) Å	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker SMART APEXII diffractometer	4585 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3698 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.968	R_int = 0.032
28987 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.115	All H-atom parameters refined
S = 1.05	Δρ_max = 0.41 e Å⁻³
4585 reflections	Δρ_min = −0.36 e Å⁻³
286 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.37232 (8)	0.96741 (8)	0.58121 (4)	0.01832 (19)
N2	0.43578 (9)	0.80090 (8)	0.70073 (5)	0.0223 (2)
O1	0.59707 (8)	0.90401 (9)	0.70207 (5)	0.0323 (2)
O2	0.25210 (8)	0.73656 (7)	0.69180 (4)	0.0293 (2)
O3	0.60527 (8)	1.01872 (8)	0.56746 (4)	0.0261 (2)
O4	0.59604 (7)	1.12962 (7)	0.64969 (4)	0.0265 (2)
F1	0.02339 (7)	0.95536 (7)	0.66222 (4)	0.0360 (2)
F2	0.01291 (10)	1.04045 (8)	0.57563 (5)	0.0519 (3)
F3	−0.11317 (8)	0.92265 (11)	0.59782 (7)	0.0708 (4)
C1	0.49344 (10)	0.89519 (10)	0.69792 (5)	0.0218 (2)
C2	0.40611 (10)	0.98226 (9)	0.68818 (5)	0.0187 (2)
C3	0.42693 (10)	1.03976 (9)	0.62520 (5)	0.0182 (2)
C4	0.25821 (9)	0.94880 (9)	0.60901 (5)	0.0180 (2)
C5	0.29053 (9)	0.92447 (9)	0.67894 (5)	0.0187 (2)
C6	0.31822 (10)	0.80982 (9)	0.69077 (5)	0.0206 (2)
C7	0.49500 (13)	0.70166 (11)	0.71063 (7)	0.0309 (3)
C8	0.55262 (10)	1.05870 (9)	0.60979 (5)	0.0197 (2)
C9	0.71865 (12)	1.14732 (14)	0.64520 (7)	0.0352 (3)
C10	−0.00083 (11)	0.94442 (12)	0.60086 (7)	0.0342 (3)
C11	0.19231 (9)	0.86470 (9)	0.57357 (5)	0.0182 (2)
C12	0.25319 (10)	0.78516 (10)	0.54317 (6)	0.0238 (2)
C13	0.19746 (11)	0.70890 (10)	0.50777 (6)	0.0246 (2)
C14	0.07863 (11)	0.70963 (10)	0.50236 (6)	0.0241 (2)
C15	0.01667 (11)	0.78587 (10)	0.53409 (6)	0.0265 (3)
C16	0.07221 (10)	0.86314 (10)	0.56912 (6)	0.0224 (2)
H4	0.2122 (13)	1.0153 (12)	0.6103 (7)	0.023 (4)*
H14	0.0394 (13)	0.6570 (12)	0.4770 (7)	0.024 (4)*
H5	0.2277 (12)	0.9465 (11)	0.7074 (7)	0.018 (3)*
H1	0.3693 (12)	0.9935 (12)	0.5427 (7)	0.021 (4)*
H3	0.3902 (13)	1.1102 (12)	0.6286 (7)	0.025 (4)*
H15	−0.0638 (14)	0.7870 (13)	0.5322 (8)	0.034 (4)*
H2	0.4071 (13)	1.0292 (13)	0.7231 (7)	0.028 (4)*
H12	0.3371 (15)	0.7847 (13)	0.5480 (8)	0.034 (4)*
H13	0.2416 (14)	0.6568 (13)	0.4868 (8)	0.032 (4)*
H73	0.5522 (17)	0.7131 (15)	0.7416 (10)	0.051 (5)*
H72	0.5263 (16)	0.6773 (15)	0.6724 (10)	0.048 (5)*
H93	0.7376 (17)	1.2026 (16)	0.6754 (9)	0.053 (5)*
H71	0.4386 (16)	0.6518 (15)	0.7264 (9)	0.043 (5)*
H92	0.7571 (18)	1.0823 (17)	0.6561 (9)	0.052 (6)*
H91	0.7395 (18)	1.1612 (16)	0.6019 (10)	0.057 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0192 (4)	0.0201 (5)	0.0156 (4)	−0.0034 (3)	−0.0001 (3)	−0.0012 (3)
N2	0.0226 (5)	0.0219 (5)	0.0223 (4)	−0.0002 (4)	−0.0016 (4)	0.0028 (4)
O1	0.0209 (4)	0.0408 (6)	0.0351 (5)	−0.0038 (4)	−0.0069 (4)	0.0116 (4)
O2	0.0306 (5)	0.0260 (5)	0.0313 (4)	−0.0092 (4)	−0.0024 (4)	0.0040 (4)
O3	0.0235 (4)	0.0328 (5)	0.0219 (4)	−0.0027 (4)	0.0024 (3)	−0.0044 (3)
O4	0.0226 (4)	0.0287 (5)	0.0282 (4)	−0.0085 (4)	0.0013 (3)	−0.0080 (4)
F1	0.0303 (4)	0.0427 (5)	0.0349 (4)	0.0047 (3)	0.0050 (3)	−0.0139 (4)
F2	0.0706 (7)	0.0358 (5)	0.0493 (6)	0.0292 (5)	−0.0191 (5)	−0.0091 (4)
F3	0.0184 (4)	0.0833 (8)	0.1107 (10)	0.0122 (5)	−0.0119 (5)	−0.0622 (8)
C1	0.0222 (5)	0.0272 (6)	0.0162 (5)	−0.0026 (4)	−0.0030 (4)	0.0019 (4)
C2	0.0199 (5)	0.0206 (5)	0.0157 (4)	−0.0035 (4)	0.0002 (4)	−0.0033 (4)
C3	0.0191 (5)	0.0176 (5)	0.0178 (4)	−0.0020 (4)	−0.0002 (4)	−0.0017 (4)
C4	0.0169 (5)	0.0184 (5)	0.0185 (5)	−0.0004 (4)	0.0001 (4)	−0.0024 (4)
C5	0.0172 (5)	0.0215 (5)	0.0174 (4)	−0.0020 (4)	0.0016 (4)	−0.0021 (4)
C6	0.0223 (5)	0.0235 (6)	0.0161 (5)	−0.0027 (4)	0.0010 (4)	0.0000 (4)
C7	0.0309 (7)	0.0268 (7)	0.0352 (7)	0.0057 (5)	−0.0003 (5)	0.0065 (5)
C8	0.0207 (5)	0.0195 (5)	0.0189 (5)	−0.0022 (4)	−0.0014 (4)	0.0009 (4)
C9	0.0232 (6)	0.0457 (9)	0.0367 (7)	−0.0127 (6)	0.0005 (5)	−0.0083 (6)
C10	0.0202 (6)	0.0376 (8)	0.0448 (8)	0.0082 (5)	−0.0101 (5)	−0.0172 (6)
C11	0.0182 (5)	0.0191 (5)	0.0174 (5)	−0.0019 (4)	−0.0003 (4)	−0.0009 (4)
C12	0.0186 (5)	0.0255 (6)	0.0274 (5)	−0.0036 (4)	0.0050 (4)	−0.0062 (4)
C13	0.0254 (6)	0.0226 (6)	0.0257 (5)	−0.0034 (5)	0.0065 (4)	−0.0061 (4)
C14	0.0262 (6)	0.0228 (6)	0.0231 (5)	−0.0045 (5)	−0.0024 (4)	−0.0039 (4)
C15	0.0198 (5)	0.0290 (6)	0.0307 (6)	0.0000 (5)	−0.0065 (5)	−0.0059 (5)
C16	0.0185 (5)	0.0234 (6)	0.0254 (5)	0.0036 (4)	−0.0044 (4)	−0.0048 (4)

Geometric parameters (Å, º) top

N1—C3	1.4578 (14)	C4—C5	1.5633 (15)
N1—C4	1.4704 (14)	C4—H4	1.002 (15)
N1—H1	0.884 (15)	C5—C6	1.5164 (17)
N2—C1	1.3766 (16)	C5—H5	0.988 (14)
N2—C6	1.3866 (15)	C7—H73	0.95 (2)
N2—C7	1.4545 (16)	C7—H72	0.94 (2)
O1—C1	1.2124 (14)	C7—H71	0.972 (19)
O2—C6	1.2089 (15)	C9—H93	0.98 (2)
O3—C8	1.2008 (14)	C9—H92	0.97 (2)
O4—C8	1.3375 (14)	C9—H91	0.97 (2)
O4—C9	1.4451 (15)	C10—C16	1.4990 (17)
F1—C10	1.3406 (17)	C11—C12	1.3942 (16)
F2—C10	1.3452 (19)	C11—C16	1.3984 (15)
F3—C10	1.3357 (16)	C12—C13	1.3886 (16)
C1—C2	1.5173 (17)	C12—H12	0.980 (17)
C2—C5	1.5437 (15)	C13—C14	1.3852 (17)
C2—C3	1.5444 (15)	C13—H13	0.950 (17)
C2—H2	0.953 (16)	C14—C15	1.3842 (18)
C3—C8	1.5157 (16)	C14—H14	0.973 (15)
C3—H3	0.997 (16)	C15—C16	1.3923 (17)
C4—C11	1.5168 (15)	C15—H15	0.936 (17)

C3—N1—C4	103.70 (8)	N2—C7—H72	110.1 (12)
C3—N1—H1	112.0 (10)	H73—C7—H72	112.3 (16)
C4—N1—H1	113.3 (9)	N2—C7—H71	107.4 (11)
C1—N2—C6	113.64 (10)	H73—C7—H71	109.5 (16)
C1—N2—C7	122.31 (11)	H72—C7—H71	110.0 (16)
C6—N2—C7	124.00 (11)	O3—C8—O4	124.67 (11)
C8—O4—C9	115.80 (10)	O3—C8—C3	125.80 (10)
O1—C1—N2	124.12 (12)	O4—C8—C3	109.51 (9)
O1—C1—C2	127.31 (11)	O4—C9—H93	106.9 (12)
N2—C1—C2	108.57 (10)	O4—C9—H92	107.7 (12)
C1—C2—C5	104.50 (9)	H93—C9—H92	110.8 (17)
C1—C2—C3	111.11 (9)	O4—C9—H91	109.7 (12)
C5—C2—C3	104.61 (9)	H93—C9—H91	115.8 (17)
C1—C2—H2	110.2 (10)	H92—C9—H91	105.6 (17)
C5—C2—H2	114.1 (10)	F3—C10—F1	105.89 (13)
C3—C2—H2	112.0 (10)	F3—C10—F2	106.58 (12)
N1—C3—C8	112.42 (9)	F1—C10—F2	105.55 (11)
N1—C3—C2	100.80 (9)	F3—C10—C16	112.82 (11)
C8—C3—C2	114.43 (9)	F1—C10—C16	112.98 (11)
N1—C3—H3	115.4 (9)	F2—C10—C16	112.44 (13)
C8—C3—H3	106.6 (9)	C12—C11—C16	117.67 (10)
C2—C3—H3	107.3 (9)	C12—C11—C4	119.15 (10)
N1—C4—C11	111.69 (9)	C16—C11—C4	123.17 (10)
N1—C4—C5	101.36 (8)	C13—C12—C11	121.52 (11)
C11—C4—C5	116.93 (9)	C13—C12—H12	121.0 (10)
N1—C4—H4	110.8 (9)	C11—C12—H12	117.4 (10)
C11—C4—H4	109.9 (9)	C14—C13—C12	120.32 (11)
C5—C4—H4	105.7 (8)	C14—C13—H13	120.2 (10)
C6—C5—C2	104.70 (9)	C12—C13—H13	119.4 (10)
C6—C5—C4	113.54 (9)	C15—C14—C13	118.85 (11)
C2—C5—C4	103.61 (9)	C15—C14—H14	120.6 (9)
C6—C5—H5	109.2 (8)	C13—C14—H14	120.5 (9)
C2—C5—H5	115.4 (8)	C14—C15—C16	121.01 (11)
C4—C5—H5	110.4 (8)	C14—C15—H15	120.6 (10)
O2—C6—N2	124.03 (11)	C16—C15—H15	118.4 (10)
O2—C6—C5	127.72 (11)	C15—C16—C11	120.57 (11)
N2—C6—C5	108.25 (9)	C15—C16—C10	117.79 (11)
N2—C7—H73	107.4 (12)	C11—C16—C10	121.63 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.884 (15)	2.363 (15)	3.1738 (13)	152.5 (13)

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅F₃N₂O₄
M_r	356.30
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	150
a, b, c (Å)	11.6168 (4), 12.7385 (5), 21.2429 (8)
V (Å³)	3143.5 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.955, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	28987, 4585, 3698
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.115, 1.05
No. of reflections	4585
No. of parameters	286
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.36

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.884 (15)	2.363 (15)	3.1738 (13)	152.5 (13)

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

This study was partially supported by the Russian Foundation for Basic Research (project Nos 11-03-00630_a, 11-03-91375-ST_a and 12-03-92005-NNS_a).

References

Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kudryavtsev, K. V. (2008). Russ. Chem. Bull. 57, 2364–2372. Web of Science CrossRef CAS Google Scholar
Kudryavtsev, K. V., Churakov, A. V. & Dogan, O. (2011). Acta Cryst. E67, o3186. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kudryavtsev, K. V. & Irkha, V. V. (2005). Molecules, 10, 755–761. Web of Science CrossRef PubMed CAS Google Scholar
Kudryavtsev, K. V. & Zagulyaeva, A. A. (2008). Russ. J. Org. Chem. 44, 378–387. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 2| February 2013| Pages o161-o162

doi:10.1107/S1600536812051471

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(1SR,3RS,3aSR,6aRS)-Methyl 5-methyl-4,6-dioxo-3-[2-(tri­fluoro­meth­yl)phen­yl]octa­hydro­pyrrolo­[3,4-c]pyrrole-1-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1SR,3RS,3aSR,6aRS)-Methyl 5-methyl-4,6-dioxo-3-[2-(trifluoromethyl)phenyl]octahydropyrrolo[3,4-c]pyrrole-1-carboxylate